A facile rearrangement of N-alkyl, N-(0 or p-nitrophenylsulfonamide)-α-amino esters

Autor:	John C. Hodges, Stephanie E. Ault-Justus, Michael W. Wilson, J. Ronald Rubin
Rok vydání:	1999
Předmět:	chemistry.chemical_classification Primary (chemistry) Amino esters Tetrabutylammonium hydroxide Organic Chemistry Ring (chemistry) Biochemistry Medicinal chemistry Metal chemistry.chemical_compound chemistry Nucleophile visual_art Drug Discovery visual_art.visual_art_medium Moiety Alkyl
Zdroj:	Tetrahedron. 55:1647-1656
ISSN:	0040-4020
DOI:	10.1016/s0040-4020(98)01209-5
Popis:	The N-alkylation of primary nitrophenylsulfonamides followed by removal of the nitrophenylsulfonamide moiety under nucleophilic conditions to provide secondary amines has become an established literature procedure. Application of this methodology with less reactive alkylating agents can give rise to side products resulting from a nitrogen to carbon transfer of the nitrophenyl ring. This side product predominates when tetrabutylammonium hydroxide is used in place of metal carbonate bases in the N-alkylation step.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::26519926479a12671c6984a61ec3796b https://doi.org/10.1016/s0040-4020(98)01209-5 Zobrazit plný text záznamu Full Text from ScienceDirect